EP0710705A1 - Pigments jaunes de diketopyrrolopyrrole - Google Patents

Pigments jaunes de diketopyrrolopyrrole Download PDF

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Publication number
EP0710705A1
EP0710705A1 EP95810665A EP95810665A EP0710705A1 EP 0710705 A1 EP0710705 A1 EP 0710705A1 EP 95810665 A EP95810665 A EP 95810665A EP 95810665 A EP95810665 A EP 95810665A EP 0710705 A1 EP0710705 A1 EP 0710705A1
Authority
EP
European Patent Office
Prior art keywords
diketopyrrolo
hydrogen
alkyl
formula
pyrroles
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP95810665A
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German (de)
English (en)
Other versions
EP0710705B1 (fr
Inventor
Bernd Dr. Lamatsch
Olof Dr. Wallquist
Ingo Schlöder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0710705A1 publication Critical patent/EP0710705A1/fr
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Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes

Definitions

  • the present invention relates to new yellow diketopyrrolopyrroles and their use as pigments.
  • 1,4-Diketopyrrolo [3,4-c] pyrroles have been known for some years as red pigments with excellent pigment properties, for example from US Pat. No. 4,415,685, where diketopyrrolopyrroles of the formula wherein R1 and R2 are isocyclic or heterocyclic radicals, preferably mono- to tetracyclic, especially mono- or bicyclic radicals, described as red pigments with high color purity, high color strength and good resistance, such as light, weather, heat and migration resistance are.
  • the good suitability of such products as pigments with an orange to, in particular, red shade is also confirmed in numerous subsequent patents, such as, for example, in US Pat. No. 4,579,949, US Pat. No. 4,720,305, US Pat. No. 4,810,802, US Pat. No. 4,783,540, US Pat .
  • the present invention accordingly relates to diketopyrrolo [3,4-c] pyrroles of the formula wherein R1 and R2 are independently hydrogen, halogen, C1-C6-alkyl, cyano or a group -OR3, -COOR3, -CON (R3) (R4), -COR3 or -N (R3) (R4) and R3 and R4 independently of one another are hydrogen, C1-C6-alkyl, unsubstituted or substituted by halogen or C1-C6-alkyl phenyl.
  • any substituents are halogen, they are e.g. for iodine, bromine, fluorine or especially chlorine.
  • C1-C6 alkyl is e.g. for methyl, ethyl, n-propyl, isopropyl, n-butyl, sec.-butyl, tert-butyl, n-pentyl, tert-amyl or n-hexyl.
  • 1,4-diketopyrrolo [3,4-c] pyrroles according to the invention are of particular interest of formula I, wherein R1 is hydrogen, chlorine, bromine, methyl, cyano, -N (R3) 2 or -OR3 means R2 is hydrogen and R3 is hydrogen or methyl.
  • the pigments of the formula I according to the invention in which R 1 and R 2 are hydrogen are preferred mean.
  • Preferred positions of substituents are the 2-, the 3-, the 6- and the 7-position on the phenanthryl system.
  • the diketopyrrolo [3,4-c] pyrroles of the formula I according to the invention can be prepared analogously to generally known processes, for example by reacting a succinic diester with a nitrile of the formula in the required ratio, as known, for example, from US Pat. No. 4,579,949.
  • nitriles of the formula II are known compounds. Should some of which are still new, they can be used in analogy to generally known methods getting produced.
  • the diketopyrrolo [3,4-c] pyrroles according to the invention can be used as pigments for coloring of high molecular weight organic material.
  • High molecular weight organic materials with the diketopyrrolo- [3,4-c] pyrroles according to the invention can be pigmented, e.g. Cellulose ethers and esters, such as Ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butyrate, natural resins or Synthetic resins, such as polymerization resins or condensation resins, such as aminoplasts, in particular urea and melamine-formaldehyde resins, alkyl resins, phenoplasts, Polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polytetrafluoroethylene, Polyamides, polyurethanes, polyesters, polyether ketones, polyphenylene oxides, rubber, Casein, silicone and silicone resins, individually or in mixtures.
  • Cellulose ethers and esters such as Ethyl cellulose, nitrocellulose, cellulose acetate, cellulose butyrate, natural resins or Synthetic
  • the aforementioned high molecular weight organic compounds can be used individually or in Mixtures as plastic masses, melts or in the form of spinning solutions, lacquers, Paint or printing inks are available. It turns out depending on the purpose as advantageous, the inventive diketopyrrolo [3,4-c] pyrrole as a toner or in Use form of preparations. Based on the high molecular weight to be pigmented The diketopyrrolo [3,4-c] pyrroles according to the invention can be used in organic material an amount of 0.01 to 30% by weight, preferably 0.1 to 10% by weight.
  • the high-molecular organic ones are used to pigment paints and printing inks Materials and the diketopyrrolo [3,4-c] pyrroles according to the invention, if appropriate together with additives such as fillers, other pigments, Siccatives or Plasticizers, in a common organic solvent or solvent mixture finely dispersed or dissolved. You can do it in such a way that you have the individual Components for themselves or several dispersed or dissolved together, and only then brings all the components together.
  • the dyeings obtained for example in plastics, fibers, paints or prints, are characterized by good general properties such as high color strength, good dispersibility, good overpainting, migration, heat, light and weather resistance, as well as with a good sheen.
  • a mixture of 1.0 g of the pigment obtained according to Example 1, 1.0 g of antioxidant (IRGANOX® 1010, CIBA-GEIGY AG) and 1000 g polyethylene HD granulate (®VESTOLEN 60-16, HUELS) is placed in a glass bottle on a Premixed roll bench. The mixture is then passed in two passages on a single-screw extruder extruded, the granules obtained in this way are injection molded (Allround Aarburg 200) sprayed into sheets at 220 ° C and pressed for 5 minutes at 180 ° C. The Press plates have strong yellow shades with good resistance.
  • 0.6 g of the pigment obtained according to Example 1 is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyltin dilaurate and 2 g of titanium dioxide are mixed and processed into a thin film on a roller mill at 160 ° C. for 15 minutes.
  • the yellow PVC film produced in this way is strong in color and lightfast.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP95810665A 1994-11-04 1995-10-27 Pigments jaunes de diketopyrrolopyrrole Expired - Lifetime EP0710705B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH330594 1994-11-04
CH3305/94 1994-11-04
CH330594 1994-11-04

Publications (2)

Publication Number Publication Date
EP0710705A1 true EP0710705A1 (fr) 1996-05-08
EP0710705B1 EP0710705B1 (fr) 1999-12-22

Family

ID=4253116

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95810665A Expired - Lifetime EP0710705B1 (fr) 1994-11-04 1995-10-27 Pigments jaunes de diketopyrrolopyrrole

Country Status (6)

Country Link
US (1) US5672716A (fr)
EP (1) EP0710705B1 (fr)
JP (1) JP3919248B2 (fr)
KR (1) KR960017668A (fr)
CA (1) CA2161997A1 (fr)
DE (1) DE59507473D1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006342167A (ja) * 2000-01-06 2006-12-21 Toray Ind Inc ジケトピロロ［３，４−ｃ］ピロール誘導体
WO2005039514A1 (fr) * 2003-10-17 2005-05-06 Ciba Specialty Chemicals Holding Inc. Formulations cosmetiques comprenant des pigments diketo-pyrrolo-pyrroles
CN1867313A (zh) * 2003-10-17 2006-11-22 西巴特殊化学制品控股公司 包含二酮二苯基吡咯并吡咯颜料的化妆品制剂
CN1867315A (zh) * 2003-10-17 2006-11-22 西巴特殊化学品控股有限公司 包含二酮基二苯基吡咯并吡咯颜料的化妆品配制物
US9751107B2 (en) * 2012-03-21 2017-09-05 Valspar Sourcing, Inc. Two-coat single cure powder coating
JP2023127878A (ja) * 2022-03-02 2023-09-14 東洋インキＳｃホールディングス株式会社 ジケトピロロピロール顔料、顔料組成物、着色組成物、カラーフィルタおよびセンサ

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4415685A (en) 1981-03-20 1983-11-15 Ciba-Geigy Corporation Process for dyeing high-molecular organic material, and novel polycyclic pigments
US4579949A (en) 1982-05-17 1986-04-01 Ciba-Geigy Corporation Preparation of pyrrolo[3,4-c]pyrroles
US4720305A (en) 1984-11-07 1988-01-19 Ciba-Geigy Corporation Mixtures of pigments
US4783540A (en) 1986-08-07 1988-11-08 Ciba-Geigy Corporation Solid solutions of pyrrolo-(3,4-C)-pyrrols
US4810802A (en) 1986-01-31 1989-03-07 Ciba-Geigy Corporation Process for the preparation of brominated pyrrolo-[3,4-c]-pyrroles and mixtures thereof
DE3908312A1 (de) * 1989-03-14 1990-09-27 Langhals Heinz Neue fluoreszierende perylen- und diketopyrrolopyrrol-farbpigmente
US5200528A (en) 1991-04-26 1993-04-06 Ciba-Geigy Corporation Diketopyrrolopyrroles

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2802338B2 (ja) * 1988-07-29 1998-09-24 リーデル―デ・ヘーン・アクチェンゲゼルシャフト 新規の１，４−ジケトンピローロピロール染料

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4415685A (en) 1981-03-20 1983-11-15 Ciba-Geigy Corporation Process for dyeing high-molecular organic material, and novel polycyclic pigments
US4579949A (en) 1982-05-17 1986-04-01 Ciba-Geigy Corporation Preparation of pyrrolo[3,4-c]pyrroles
US4720305A (en) 1984-11-07 1988-01-19 Ciba-Geigy Corporation Mixtures of pigments
US4810802A (en) 1986-01-31 1989-03-07 Ciba-Geigy Corporation Process for the preparation of brominated pyrrolo-[3,4-c]-pyrroles and mixtures thereof
US4783540A (en) 1986-08-07 1988-11-08 Ciba-Geigy Corporation Solid solutions of pyrrolo-(3,4-C)-pyrrols
DE3908312A1 (de) * 1989-03-14 1990-09-27 Langhals Heinz Neue fluoreszierende perylen- und diketopyrrolopyrrol-farbpigmente
US5200528A (en) 1991-04-26 1993-04-06 Ciba-Geigy Corporation Diketopyrrolopyrroles

Also Published As

Publication number Publication date
JPH08245897A (ja) 1996-09-24
US5672716A (en) 1997-09-30
DE59507473D1 (de) 2000-01-27
KR960017668A (ko) 1996-06-17
CA2161997A1 (fr) 1996-05-05
EP0710705B1 (fr) 1999-12-22
JP3919248B2 (ja) 2007-05-23

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